# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ddd



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C22 H32 Br4 Cu4 N8'

_chemical_formula_weight         982.36



loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source










C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Orthorhombic

_symmetry_space_group_name_H-M   Pnn2



loop_

_symmetry_equiv_pos_as_xyz




'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1/2'



_cell_length_a                   9.568(3)

_cell_length_b                   17.673(6)

_cell_length_c                   9.560(3)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.00

_cell_angle_gamma                90.00

_cell_volume                     1616.5(9)

_cell_formula_units_Z            2

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    2565

_cell_measurement_theta_min      2.42

_cell_measurement_theta_max      24.02



_exptl_crystal_description       block

_exptl_crystal_colour            yellow

_exptl_crystal_size_max          0.23

_exptl_crystal_size_mid          0.15

_exptl_crystal_size_min          0.11

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    2.018

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             952

_exptl_absorpt_coefficient_mu    7.566

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.2750

_exptl_absorpt_correction_T_max  0.4899

_exptl_absorpt_process_details   sadabs



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      296(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            6526

_diffrn_reflns_av_R_equivalents  0.0254

_diffrn_reflns_av_sigmaI/netI    0.0466

_diffrn_reflns_limit_h_min       -11

_diffrn_reflns_limit_h_max       11

_diffrn_reflns_limit_k_min       -21

_diffrn_reflns_limit_k_max       15

_diffrn_reflns_limit_l_min       -11

_diffrn_reflns_limit_l_max       10

_diffrn_reflns_theta_min         2.42

_diffrn_reflns_theta_max         25.49

_reflns_number_total             2875

_reflns_number_gt                2557

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

 Refinement of F² against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F², conventional R-factors R are based

 on F, with F set to zero for negative F². The threshold expression of

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F² are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0045P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881'

_refine_ls_abs_structure_Flack   0.019(10)

_refine_ls_number_reflns         2875

_refine_ls_number_parameters     174

_refine_ls_number_restraints     1

_refine_ls_R_factor_all          0.0335

_refine_ls_R_factor_gt           0.0265

_refine_ls_wR_factor_ref         0.0534

_refine_ls_wR_factor_gt          0.0513

_refine_ls_goodness_of_fit_ref   1.014

_refine_ls_restrained_S_all      1.013

_refine_ls_shift/su_max          0.001

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group



































Cu1 Cu 0.95753(7) 0.92235(4) 0.27713(7) 0.06033(19) Uani 1 1 d . . .
Cu2 Cu 1.15954(6) 0.97065(4) 0.09065(7) 0.06115(19) Uani 1 1 d . . .
N1 N 0.8574(4) 0.8444(2) 0.3894(4) 0.0477(10) Uani 1 1 d . . .
N2 N 0.7705(4) 0.7789(2) 0.5628(4) 0.0498(11) Uani 1 1 d . . .
N3 N 0.4636(3) 0.9007(2) 0.8095(4) 0.0418(9) Uani 1 1 d . . .
N4 N 0.2901(3) 0.9398(2) 0.9388(4) 0.0419(9) Uani 1 1 d . . .
Br1 Br 0.92244(4) 0.89384(2) 0.02405(5) 0.04025(11) Uani 1 1 d . . .
Br2 Br 1.20268(5) 0.95575(3) 0.33911(5) 0.04842(13) Uani 1 1 d . . .
C1 C 0.8614(4) 0.8317(3) 0.5220(6) 0.0479(11) Uani 1 1 d . . .
C2 C 0.6993(6) 0.7555(3) 0.4396(6) 0.0665(16) Uani 1 1 d . . .
H2 H 0.6292 0.7193 0.4326 0.080 Uiso 1 1 calc R . .
C3 C 0.7543(5) 0.7963(3) 0.3365(6) 0.0611(13) Uani 1 1 d . . .
H3 H 0.7280 0.7932 0.2431 0.073 Uiso 1 1 calc R . .
C4 C 0.9605(6) 0.8687(4) 0.6161(6) 0.0765(17) Uani 1 1 d . . .
H4A H 0.9699 0.8393 0.7000 0.115 Uiso 1 1 calc R . .
H4B H 0.9269 0.9183 0.6392 0.115 Uiso 1 1 calc R . .
H4C H 1.0498 0.8727 0.5709 0.115 Uiso 1 1 calc R . .
C5 C 0.7319(5) 0.7516(3) 0.6981(6) 0.0637(15) Uani 1 1 d . . .
H5A H 0.8058 0.7637 0.7638 0.076 Uiso 1 1 calc R . .
H5B H 0.7234 0.6969 0.6942 0.076 Uiso 1 1 calc R . .
C6 C 0.5952(5) 0.7847(3) 0.7518(6) 0.0629(16) Uani 1 1 d . . .
H6A H 0.5206 0.7712 0.6878 0.076 Uiso 1 1 calc R . .
H6B H 0.5738 0.7623 0.8420 0.076 Uiso 1 1 calc R . .
C7 C 0.5990(4) 0.8690(3) 0.7670(6) 0.0498(12) Uani 1 1 d . . .
H7A H 0.6689 0.8824 0.8361 0.060 Uiso 1 1 calc R . .
H7B H 0.6267 0.8913 0.6785 0.060 Uiso 1 1 calc R . .
C8 C 0.4184(4) 0.9109(2) 0.9401(5) 0.0393(10) Uani 1 1 d . . .
C9 C 0.3602(5) 0.9225(3) 0.7195(6) 0.0514(12) Uani 1 1 d . . .
H9 H 0.3625 0.9213 0.6223 0.062 Uiso 1 1 calc R . .
C10 C 0.2544(5) 0.9460(3) 0.8011(5) 0.0494(13) Uani 1 1 d . . .
H10 H 0.1691 0.9639 0.7684 0.059 Uiso 1 1 calc R . .
C11 C 0.4987(4) 0.8932(3) 1.0689(5) 0.0526(13) Uani 1 1 d . . .
H11A H 0.4528 0.9152 1.1483 0.079 Uiso 1 1 calc R . .
H11B H 0.5914 0.9136 1.0609 0.079 Uiso 1 1 calc R . .
H11C H 0.5040 0.8393 1.0806 0.079 Uiso 1 1 calc R . .






_geom_special_details            
;

 All esds (except the esd in the dihedral angle between two l.s. planes)

 are estimated using the full covariance matrix.  The cell esds are taken

 into account individually in the estimation of esds in distances, angles

 and torsion angles; correlations between esds in cell parameters are only

 used when they are defined by crystal symmetry.  An approximate (isotropic)

 treatment of cell esds is used for estimating esds involving l.s. planes.

;



loop_

_geom_bond_atom_site_label_1

_geom_bond_atom_site_label_2

_geom_bond_distance

_geom_bond_site_symmetry_2

_geom_bond_publ_flag















































Cu1 N1 1.992(4) . ?
Cu1 Br2 2.4903(11) . ?
Cu1 Br1 2.4939(12) . ?
Cu1 Br2 2.7097(11) 2_775 ?
Cu1 Cu2 2.7645(11) . ?
Cu1 Cu2 2.8299(11) 2_775 ?
Cu1 Cu1 2.8625(16) 2_775 ?
Cu2 N4 1.992(4) 1_654 ?
Cu2 Br2 2.4251(11) . ?
Cu2 Br1 2.5991(11) 2_775 ?
Cu2 Br1 2.7192(10) . ?
Cu2 Cu1 2.8299(11) 2_775 ?
N1 C1 1.289(6) . ?
N1 C3 1.397(6) . ?
N2 C1 1.335(6) . ?
N2 C2 1.422(7) . ?
N2 C5 1.429(6) . ?
N3 C8 1.333(6) . ?
N3 C9 1.366(6) . ?
N3 C7 1.469(5) . ?
N4 C8 1.329(5) . ?
N4 C10 1.365(6) . ?
N4 Cu2 1.992(4) 1_456 ?
Br1 Cu2 2.5991(11) 2_775 ?
Br2 Cu1 2.7097(11) 2_775 ?
C1 C4 1.461(7) . ?
C2 C3 1.329(7) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.522(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.497(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C11 1.485(6) . ?
C9 C10 1.343(7) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?



loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle_publ_flag






































































































N1 Cu1 Br2 119.26(12) . . ?
N1 Cu1 Br1 108.55(12) . . ?
Br2 Cu1 Br1 113.92(3) . . ?
N1 Cu1 Br2 99.22(11) . 2_775 ?
Br2 Cu1 Br2 107.00(3) . 2_775 ?
Br1 Cu1 Br2 107.25(3) . 2_775 ?
N1 Cu1 Cu2 153.79(11) . . ?
Br2 Cu1 Cu2 54.67(3) . . ?
Br1 Cu1 Cu2 62.03(3) . . ?
Br2 Cu1 Cu2 106.92(3) 2_775 . ?
N1 Cu1 Cu2 127.68(12) . 2_775 ?
Br2 Cu1 Cu2 111.36(3) . 2_775 ?
Br1 Cu1 Cu2 58.03(3) . 2_775 ?
Br2 Cu1 Cu2 51.87(3) 2_775 2_775 ?
Cu2 Cu1 Cu2 70.38(4) . 2_775 ?
N1 Cu1 Cu1 143.11(11) . 2_775 ?
Br2 Cu1 Cu1 60.35(2) . 2_775 ?
Br1 Cu1 Cu1 103.408(19) . 2_775 ?
Br2 Cu1 Cu1 53.01(3) 2_775 2_775 ?
Cu2 Cu1 Cu1 60.36(2) . 2_775 ?
Cu2 Cu1 Cu1 58.11(3) 2_775 2_775 ?
N4 Cu2 Br2 125.26(11) 1_654 . ?
N4 Cu2 Br1 105.27(11) 1_654 2_775 ?
Br2 Cu2 Br1 113.04(3) . 2_775 ?
N4 Cu2 Br1 102.47(11) 1_654 . ?
Br2 Cu2 Br1 108.49(3) . . ?
Br1 Cu2 Br1 98.67(3) 2_775 . ?
N4 Cu2 Cu1 145.48(11) 1_654 . ?
Br2 Cu2 Cu1 56.90(3) . . ?
Br1 Cu2 Cu1 103.38(3) 2_775 . ?
Br1 Cu2 Cu1 54.09(3) . . ?
N4 Cu2 Cu1 152.96(11) 1_654 2_775 ?
Br2 Cu2 Cu1 61.51(3) . 2_775 ?
Br1 Cu2 Cu1 54.49(3) 2_775 2_775 ?
Br1 Cu2 Cu1 98.68(3) . 2_775 ?
Cu1 Cu2 Cu1 61.54(3) . 2_775 ?
C1 N1 C3 105.7(4) . . ?
C1 N1 Cu1 129.5(3) . . ?
C3 N1 Cu1 124.5(4) . . ?
C1 N2 C2 105.9(4) . . ?
C1 N2 C5 132.0(5) . . ?
C2 N2 C5 121.8(4) . . ?
C8 N3 C9 108.5(4) . . ?
C8 N3 C7 126.6(4) . . ?
C9 N3 C7 124.9(4) . . ?
C8 N4 C10 105.7(4) . . ?
C8 N4 Cu2 132.7(3) . 1_456 ?
C10 N4 Cu2 121.6(3) . 1_456 ?
Cu1 Br1 Cu2 67.47(3) . 2_775 ?
Cu1 Br1 Cu2 63.88(2) . . ?
Cu2 Br1 Cu2 74.60(3) 2_775 . ?
Cu2 Br2 Cu1 68.43(3) . . ?
Cu2 Br2 Cu1 66.62(2) . 2_775 ?
Cu1 Br2 Cu1 66.65(3) . 2_775 ?
N1 C1 N2 112.9(5) . . ?
N1 C1 C4 123.2(5) . . ?
N2 C1 C4 123.8(5) . . ?
C3 C2 N2 105.5(4) . . ?
C3 C2 H2 127.3 . . ?
N2 C2 H2 127.3 . . ?
C2 C3 N1 110.0(5) . . ?
C2 C3 H3 125.0 . . ?
N1 C3 H3 125.0 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C6 113.5(4) . . ?
N2 C5 H5A 108.9 . . ?
C6 C5 H5A 108.9 . . ?
N2 C5 H5B 108.9 . . ?
C6 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C7 C6 C5 113.2(4) . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
N3 C7 C6 112.7(4) . . ?
N3 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
N3 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
N4 C8 N3 110.0(4) . . ?
N4 C8 C11 124.5(4) . . ?
N3 C8 C11 125.5(4) . . ?
C10 C9 N3 105.5(5) . . ?
C10 C9 H9 127.3 . . ?
N3 C9 H9 127.3 . . ?
C9 C10 N4 110.3(4) . . ?
C9 C10 H10 124.9 . . ?
N4 C10 H10 124.9 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?



loop_

_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag












































































































N1 Cu1 Cu2 N4 20.4(3) . . . 1_654 ?
Br2 Cu1 Cu2 N4 105.6(2) . . . 1_654 ?
Br1 Cu1 Cu2 N4 -54.37(19) . . . 1_654 ?
Br2 Cu1 Cu2 N4 -155.29(19) 2_775 . . 1_654 ?
Cu2 Cu1 Cu2 N4 -117.82(19) 2_775 . . 1_654 ?
Cu1 Cu1 Cu2 N4 178.4(2) 2_775 . . 1_654 ?
N1 Cu1 Cu2 Br2 -85.2(3) . . . . ?
Br1 Cu1 Cu2 Br2 -159.93(3) . . . . ?
Br2 Cu1 Cu2 Br2 99.15(3) 2_775 . . . ?
Cu2 Cu1 Cu2 Br2 136.62(4) 2_775 . . . ?
Cu1 Cu1 Cu2 Br2 72.88(2) 2_775 . . . ?
N1 Cu1 Cu2 Br1 165.8(3) . . . 2_775 ?
Br2 Cu1 Cu2 Br1 -108.97(3) . . . 2_775 ?
Br1 Cu1 Cu2 Br1 91.09(3) . . . 2_775 ?
Br2 Cu1 Cu2 Br1 -9.82(4) 2_775 . . 2_775 ?
Cu2 Cu1 Cu2 Br1 27.65(3) 2_775 . . 2_775 ?
Cu1 Cu1 Cu2 Br1 -36.09(3) 2_775 . . 2_775 ?
N1 Cu1 Cu2 Br1 74.7(3) . . . . ?
Br2 Cu1 Cu2 Br1 159.93(3) . . . . ?
Br2 Cu1 Cu2 Br1 -100.92(3) 2_775 . . . ?
Cu2 Cu1 Cu2 Br1 -63.45(3) 2_775 . . . ?
Cu1 Cu1 Cu2 Br1 -127.18(3) 2_775 . . . ?
N1 Cu1 Cu2 Cu1 -158.1(3) . . . 2_775 ?
Br2 Cu1 Cu2 Cu1 -72.88(2) . . . 2_775 ?
Br1 Cu1 Cu2 Cu1 127.18(3) . . . 2_775 ?
Br2 Cu1 Cu2 Cu1 26.26(3) 2_775 . . 2_775 ?
Cu2 Cu1 Cu2 Cu1 63.74(3) 2_775 . . 2_775 ?
Br2 Cu1 N1 C1 37.8(5) . . . . ?
Br1 Cu1 N1 C1 170.5(4) . . . . ?
Br2 Cu1 N1 C1 -77.7(4) 2_775 . . . ?
Cu2 Cu1 N1 C1 106.5(4) . . . . ?
Cu2 Cu1 N1 C1 -126.0(4) 2_775 . . . ?
Cu1 Cu1 N1 C1 -40.8(5) 2_775 . . . ?
Br2 Cu1 N1 C3 -149.4(3) . . . . ?
Br1 Cu1 N1 C3 -16.7(4) . . . . ?
Br2 Cu1 N1 C3 95.1(4) 2_775 . . . ?
Cu2 Cu1 N1 C3 -80.7(5) . . . . ?
Cu2 Cu1 N1 C3 46.8(4) 2_775 . . . ?
Cu1 Cu1 N1 C3 132.1(3) 2_775 . . . ?
N1 Cu1 Br1 Cu2 123.41(12) . . . 2_775 ?
Br2 Cu1 Br1 Cu2 -101.12(4) . . . 2_775 ?
Br2 Cu1 Br1 Cu2 17.08(2) 2_775 . . 2_775 ?
Cu2 Cu1 Br1 Cu2 -83.29(3) . . . 2_775 ?
Cu1 Cu1 Br1 Cu2 -37.91(4) 2_775 . . 2_775 ?
N1 Cu1 Br1 Cu2 -153.30(12) . . . . ?
Br2 Cu1 Br1 Cu2 -17.83(3) . . . . ?
Br2 Cu1 Br1 Cu2 100.38(4) 2_775 . . . ?
Cu2 Cu1 Br1 Cu2 83.29(3) 2_775 . . . ?
Cu1 Cu1 Br1 Cu2 45.39(3) 2_775 . . . ?
N4 Cu2 Br1 Cu1 151.86(12) 1_654 . . . ?
Br2 Cu2 Br1 Cu1 17.64(3) . . . . ?
Br1 Cu2 Br1 Cu1 -100.29(3) 2_775 . . . ?
Cu1 Cu2 Br1 Cu1 -45.12(3) 2_775 . . . ?
N4 Cu2 Br1 Cu2 -136.05(11) 1_654 . . 2_775 ?
Br2 Cu2 Br1 Cu2 89.73(3) . . . 2_775 ?
Br1 Cu2 Br1 Cu2 -28.20(4) 2_775 . . 2_775 ?
Cu1 Cu2 Br1 Cu2 72.09(2) . . . 2_775 ?
Cu1 Cu2 Br1 Cu2 26.97(3) 2_775 . . 2_775 ?
N4 Cu2 Br2 Cu1 -138.05(14) 1_654 . . . ?
Br1 Cu2 Br2 Cu1 91.32(3) 2_775 . . . ?
Br1 Cu2 Br2 Cu1 -17.04(3) . . . . ?
Cu1 Cu2 Br2 Cu1 72.93(3) 2_775 . . . ?
N4 Cu2 Br2 Cu1 149.02(14) 1_654 . . 2_775 ?
Br1 Cu2 Br2 Cu1 18.39(3) 2_775 . . 2_775 ?
Br1 Cu2 Br2 Cu1 -89.97(4) . . . 2_775 ?
Cu1 Cu2 Br2 Cu1 -72.93(3) . . . 2_775 ?
N1 Cu1 Br2 Cu2 149.71(13) . . . . ?
Br1 Cu1 Br2 Cu2 19.36(3) . . . . ?
Br2 Cu1 Br2 Cu2 -98.99(4) 2_775 . . . ?
Cu2 Cu1 Br2 Cu2 -44.00(4) 2_775 . . . ?
Cu1 Cu1 Br2 Cu2 -72.90(2) 2_775 . . . ?
N1 Cu1 Br2 Cu1 -137.39(13) . . . 2_775 ?
Br1 Cu1 Br2 Cu1 92.26(3) . . . 2_775 ?
Br2 Cu1 Br2 Cu1 -26.09(4) 2_775 . . 2_775 ?
Cu2 Cu1 Br2 Cu1 72.90(2) . . . 2_775 ?
Cu2 Cu1 Br2 Cu1 28.90(4) 2_775 . . 2_775 ?
C3 N1 C1 N2 0.4(5) . . . . ?
Cu1 N1 C1 N2 174.3(3) . . . . ?
C3 N1 C1 C4 177.4(5) . . . . ?
Cu1 N1 C1 C4 -8.8(7) . . . . ?
C2 N2 C1 N1 -0.3(5) . . . . ?
C5 N2 C1 N1 -174.4(5) . . . . ?
C2 N2 C1 C4 -177.3(5) . . . . ?
C5 N2 C1 C4 8.6(8) . . . . ?
C1 N2 C2 C3 0.1(5) . . . . ?
C5 N2 C2 C3 174.9(4) . . . . ?
N2 C2 C3 N1 0.1(6) . . . . ?
C1 N1 C3 C2 -0.3(6) . . . . ?
Cu1 N1 C3 C2 -174.6(4) . . . . ?
C1 N2 C5 C6 100.4(6) . . . . ?
C2 N2 C5 C6 -72.8(6) . . . . ?
N2 C5 C6 C7 -60.8(7) . . . . ?
C8 N3 C7 C6 89.0(6) . . . . ?
C9 N3 C7 C6 -88.5(6) . . . . ?
C5 C6 C7 N3 176.0(4) . . . . ?
C10 N4 C8 N3 1.3(5) . . . . ?
Cu2 N4 C8 N3 -179.0(3) 1_456 . . . ?
C10 N4 C8 C11 -179.0(4) . . . . ?
Cu2 N4 C8 C11 0.7(7) 1_456 . . . ?
C9 N3 C8 N4 -1.1(5) . . . . ?
C7 N3 C8 N4 -179.0(4) . . . . ?
C9 N3 C8 C11 179.2(4) . . . . ?
C7 N3 C8 C11 1.4(7) . . . . ?
C8 N3 C9 C10 0.4(5) . . . . ?
C7 N3 C9 C10 178.3(4) . . . . ?
N3 C9 C10 N4 0.4(6) . . . . ?
C8 N4 C10 C9 -1.1(5) . . . . ?
Cu2 N4 C10 C9 179.2(3) 1_456 . . . ?



_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        25.49

_diffrn_measured_fraction_theta_full 0.999

_refine_diff_density_max         0.311

_refine_diff_density_min         -0.329

_refine_diff_density_rms         0.063

_database_code_depnum_ccdc_archive 'CCDC 995971'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_aa

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 Cd N4 O4 S'
_chemical_formula_weight         486.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   9.2703(14)
_cell_length_b                   13.966(2)
_cell_length_c                   14.650(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1896.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2141
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      23.49

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    1.292
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.644
_exptl_absorpt_correction_T_max  0.803
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5986
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2861
_reflns_number_gt                2345
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0110P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_number_reflns         2861
_refine_ls_number_parameters     246
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0574
_refine_ls_wR_factor_gt          0.0556
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.13237(3) 0.46675(2) 0.90337(4) 0.04328(11) Uani 1 1 d . . .
S1 S 0.57049(16) 0.54967(10) 0.69824(11) 0.0498(4) Uani 1 1 d . . .
O1 O 0.7513(5) 0.6693(3) 0.4869(3) 0.0797(15) Uani 1 1 d . . .
O2 O 0.7702(5) 0.5272(4) 0.5443(3) 0.0778(14) Uani 1 1 d . . .
O3 O 0.2146(5) 0.6151(3) 0.8241(4) 0.0781(15) Uani 1 1 d . . .
O4 O 0.3486(4) 0.4878(3) 0.8283(3) 0.0661(13) Uani 1 1 d . . .
C1 C 0.7210(7) 0.6096(5) 0.5450(4) 0.0498(15) Uani 1 1 d . . .
C2 C 0.6110(6) 0.6323(4) 0.6147(4) 0.0436(14) Uani 1 1 d . . .
C3 C 0.5164(7) 0.7061(4) 0.6191(4) 0.0599(18) Uani 1 1 d . . .
H3 H 0.5210 0.7586 0.5801 0.072 Uiso 1 1 calc R . .
C4 C 0.4105(6) 0.6969(4) 0.6876(4) 0.0550(17) Uani 1 1 d . . .
H4 H 0.3396 0.7424 0.6991 0.066 Uiso 1 1 calc R . .
C5 C 0.4245(6) 0.6130(4) 0.7352(4) 0.0410(13) Uani 1 1 d . . .
C6 C 0.3220(6) 0.5712(4) 0.8013(4) 0.0442(14) Uani 1 1 d . . .
C7 C -0.0469(8) 0.4286(5) 0.7262(5) 0.075(2) Uani 1 1 d . . .
H7 H -0.0541 0.4949 0.7222 0.090 Uiso 1 1 calc R . .
C8 C -0.1033(8) 0.3675(5) 0.6658(5) 0.075(2) Uani 1 1 d . . .
H8 H -0.1547 0.3827 0.6132 0.090 Uiso 1 1 calc R . .
C9 C 0.0076(6) 0.2880(4) 0.7746(4) 0.0480(15) Uani 1 1 d . . .
C10 C 0.0649(7) 0.2087(4) 0.8299(4) 0.0638(18) Uani 1 1 d . . .
H10A H 0.1235 0.2339 0.8782 0.096 Uiso 1 1 calc R . .
H10B H 0.1222 0.1674 0.7920 0.096 Uiso 1 1 calc R . .
H10C H -0.0137 0.1729 0.8555 0.096 Uiso 1 1 calc R . .
C11 C -0.1119(6) 0.1889(4) 0.6484(4) 0.0530(16) Uani 1 1 d . . .
H11A H -0.2134 0.1919 0.6326 0.064 Uiso 1 1 calc R . .
H11B H -0.0975 0.1340 0.6880 0.064 Uiso 1 1 calc R . .
C12 C -0.0240(7) 0.1769(5) 0.5634(4) 0.0675(19) Uani 1 1 d . . .
H12A H 0.0766 0.1704 0.5804 0.081 Uiso 1 1 calc R . .
H12B H -0.0329 0.2346 0.5269 0.081 Uiso 1 1 calc R . .
C13 C -0.0662(6) 0.0919(6) 0.5051(5) 0.071(2) Uani 1 1 d . . .
H13A H 0.0011 0.0867 0.4547 0.086 Uiso 1 1 calc R . .
H13B H -0.0574 0.0341 0.5415 0.086 Uiso 1 1 calc R . .
C14 C -0.2631(5) 0.1660(4) 0.4113(5) 0.0532(14) Uani 1 1 d . . .
H14 H -0.2132 0.2200 0.3917 0.064 Uiso 1 1 calc R . .
C15 C -0.3980(6) 0.1416(4) 0.3886(5) 0.0490(18) Uani 1 1 d . . .
H15 H -0.4584 0.1766 0.3505 0.059 Uiso 1 1 calc R . .
C16 C -0.3195(7) 0.0325(4) 0.4785(5) 0.0550(16) Uani 1 1 d . . .
C17 C -0.3094(8) -0.0563(5) 0.5353(6) 0.099(3) Uani 1 1 d . . .
H17A H -0.4025 -0.0862 0.5388 0.148 Uiso 1 1 calc R . .
H17B H -0.2774 -0.0399 0.5956 0.148 Uiso 1 1 calc R . .
H17C H -0.2419 -0.0998 0.5080 0.148 Uiso 1 1 calc R . .
N1 N 0.0229(5) 0.3807(3) 0.7946(3) 0.0548(13) Uani 1 1 d . . .
N2 N -0.0698(5) 0.2775(3) 0.6974(4) 0.0548(13) Uani 1 1 d . . .
N3 N -0.2128(5) 0.0971(3) 0.4685(3) 0.0484(12) Uani 1 1 d . . .
N4 N -0.4332(5) 0.0566(3) 0.4306(3) 0.0454(13) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N1 2.239(5) . ?
Cd1 O2 2.255(4) 2_665 ?
Cd1 N4 2.267(4) 4_455 ?
Cd1 O4 2.305(4) . ?
Cd1 O3 2.495(4) . ?
Cd1 O1 2.504(5) 2_665 ?
Cd1 C1 2.700(6) 2_665 ?
S1 C5 1.705(5) . ?
S1 C2 1.723(6) . ?
O1 C1 1.224(7) . ?
O1 Cd1 2.504(5) 2_664 ?
O2 C1 1.238(7) . ?
O2 Cd1 2.255(4) 2_664 ?
O3 C6 1.217(6) . ?
O4 C6 1.254(7) . ?
C1 C2 1.478(8) . ?
C1 Cd1 2.700(6) 2_664 ?
C2 C3 1.355(8) . ?
C3 C4 1.410(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.477(8) . ?
C7 C8 1.336(8) . ?
C7 N1 1.369(7) . ?
C7 H7 0.9300 . ?
C8 N2 1.375(7) . ?
C8 H8 0.9300 . ?
C9 N1 1.335(7) . ?
C9 N2 1.348(7) . ?
C9 C10 1.471(7) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 N2 1.483(7) . ?
C11 C12 1.498(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.514(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N3 1.463(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.338(7) . ?
C14 N3 1.359(7) . ?
C14 H14 0.9300 . ?
C15 N4 1.377(6) . ?
C15 H15 0.9300 . ?
C16 N4 1.310(7) . ?
C16 N3 1.347(7) . ?
C16 C17 1.496(9) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N4 Cd1 2.267(4) 4_444 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cd1 O2 148.53(18) . 2_665 ?
N1 Cd1 N4 93.05(16) . 4_455 ?
O2 Cd1 N4 98.29(16) 2_665 4_455 ?
N1 Cd1 O4 97.09(18) . . ?
O2 Cd1 O4 94.81(19) 2_665 . ?
N4 Cd1 O4 136.18(15) 4_455 . ?
N1 Cd1 O3 104.66(18) . . ?
O2 Cd1 O3 105.86(18) 2_665 . ?
N4 Cd1 O3 82.60(15) 4_455 . ?
O4 Cd1 O3 53.58(14) . . ?
N1 Cd1 O1 97.79(16) . 2_665 ?
O2 Cd1 O1 53.73(15) 2_665 2_665 ?
N4 Cd1 O1 133.19(16) 4_455 2_665 ?
O4 Cd1 O1 87.43(16) . 2_665 ?
O3 Cd1 O1 136.56(15) . 2_665 ?
N1 Cd1 C1 124.26(19) . 2_665 ?
O2 Cd1 C1 27.06(16) 2_665 2_665 ?
N4 Cd1 C1 119.54(18) 4_455 2_665 ?
O4 Cd1 C1 88.81(17) . 2_665 ?
O3 Cd1 C1 122.15(18) . 2_665 ?
O1 Cd1 C1 26.87(15) 2_665 2_665 ?
C5 S1 C2 92.9(3) . . ?
C1 O1 Cd1 85.6(4) . 2_664 ?
C1 O2 Cd1 96.9(4) . 2_664 ?
C6 O3 Cd1 87.6(4) . . ?
C6 O4 Cd1 95.6(4) . . ?
O1 C1 O2 122.8(6) . . ?
O1 C1 C2 119.6(6) . . ?
O2 C1 C2 117.4(6) . . ?
O1 C1 Cd1 67.6(3) . 2_664 ?
O2 C1 Cd1 56.0(3) . 2_664 ?
C2 C1 Cd1 164.4(4) . 2_664 ?
C3 C2 C1 130.0(6) . . ?
C3 C2 S1 109.6(5) . . ?
C1 C2 S1 119.8(5) . . ?
C2 C3 C4 114.5(6) . . ?
C2 C3 H3 122.8 . . ?
C4 C3 H3 122.8 . . ?
C5 C4 C3 112.0(5) . . ?
C5 C4 H4 124.0 . . ?
C3 C4 H4 124.0 . . ?
C4 C5 C6 127.6(5) . . ?
C4 C5 S1 110.9(4) . . ?
C6 C5 S1 121.0(4) . . ?
O3 C6 O4 122.9(6) . . ?
O3 C6 C5 120.5(6) . . ?
O4 C6 C5 116.5(5) . . ?
C8 C7 N1 111.0(6) . . ?
C8 C7 H7 124.5 . . ?
N1 C7 H7 124.5 . . ?
C7 C8 N2 105.8(6) . . ?
C7 C8 H8 127.1 . . ?
N2 C8 H8 127.1 . . ?
N1 C9 N2 110.3(5) . . ?
N1 C9 C10 124.8(5) . . ?
N2 C9 C10 124.9(5) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 110.6(5) . . ?
N2 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C13 114.5(5) . . ?
C11 C12 H12A 108.6 . . ?
C13 C12 H12A 108.6 . . ?
C11 C12 H12B 108.6 . . ?
C13 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
N3 C13 C12 114.1(6) . . ?
N3 C13 H13A 108.7 . . ?
C12 C13 H13A 108.7 . . ?
N3 C13 H13B 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 N3 107.1(5) . . ?
C15 C14 H14 126.5 . . ?
N3 C14 H14 126.5 . . ?
C14 C15 N4 109.3(5) . . ?
C14 C15 H15 125.4 . . ?
N4 C15 H15 125.4 . . ?
N4 C16 N3 111.1(5) . . ?
N4 C16 C17 124.1(6) . . ?
N3 C16 C17 124.8(6) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C9 N1 C7 105.2(5) . . ?
C9 N1 Cd1 136.5(4) . . ?
C7 N1 Cd1 118.2(4) . . ?
C9 N2 C8 107.7(5) . . ?
C9 N2 C11 129.5(5) . . ?
C8 N2 C11 122.7(5) . . ?
C16 N3 C14 106.9(5) . . ?
C16 N3 C13 127.5(6) . . ?
C14 N3 C13 125.5(5) . . ?
C16 N4 C15 105.6(5) . . ?
C16 N4 Cd1 127.4(4) . 4_444 ?
C15 N4 Cd1 126.3(4) . 4_444 ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 995972'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 Cd N3 O4 S'
_chemical_formula_weight         496.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   9.4781(10)
_cell_length_b                   13.8347(14)
_cell_length_c                   15.4666(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2028.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5368
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      28.01

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             996
_exptl_absorpt_coefficient_mu    1.209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.693
_exptl_absorpt_correction_T_max  0.834
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10393
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         25.49
_reflns_number_total             3520
_reflns_number_gt                3244
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0312P)²+1.3139P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_number_reflns         3520
_refine_ls_number_parameters     250
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0627
_refine_ls_wR_factor_gt          0.0602
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.14826(2) 0.519619(16) 0.927916(19) 0.03490(8) Uani 1 1 d . . .
S1 S 0.44542(12) 0.53079(8) 1.21143(7) 0.0462(3) Uani 1 1 d . . .
O1 O 0.2371(4) 0.6475(3) 1.0207(2) 0.0734(10) Uani 1 1 d . . .
O2 O 0.2590(4) 0.4953(3) 1.06025(19) 0.0548(8) Uani 1 1 d . . .
O3 O 0.7799(3) 0.6191(2) 1.3352(2) 0.0609(9) Uani 1 1 d . . .
O4 O 0.6423(4) 0.4932(2) 1.3526(3) 0.0592(9) Uiso 1 1 d . . .
N1 N 0.0539(4) 0.6378(2) 0.8459(2) 0.0430(8) Uani 1 1 d . . .
N3 N -0.2229(4) 0.8977(3) 0.4700(2) 0.0444(8) Uani 1 1 d . . .
N4 N -0.4425(3) 0.9397(2) 0.4425(2) 0.0403(8) Uani 1 1 d . . .
C1 C 0.2870(5) 0.5838(4) 1.0683(3) 0.0496(11) Uani 1 1 d . . .
C2 C 0.3939(5) 0.6120(3) 1.1340(3) 0.0446(10) Uani 1 1 d . . .
C3 C 0.4728(6) 0.6940(3) 1.1379(3) 0.0650(14) Uani 1 1 d . . .
H3 H 0.4592 0.7468 1.1016 0.078 Uiso 1 1 calc R . .
C4 C 0.5772(6) 0.6906(3) 1.2027(3) 0.0563(12) Uani 1 1 d . . .
H4 H 0.6407 0.7405 1.2130 0.068 Uiso 1 1 calc R . .
C5 C 0.5755(4) 0.6075(3) 1.2482(2) 0.0378(9) Uani 1 1 d . . .
C6 C 0.6720(5) 0.5725(3) 1.3164(3) 0.0417(10) Uani 1 1 d . . .
C7 C -0.0365(6) 0.5341(3) 0.7261(3) 0.0606(14) Uani 1 1 d . . .
H7A H 0.0486 0.4977 0.7345 0.091 Uiso 1 1 calc R . .
H7B H -0.0474 0.5488 0.6658 0.091 Uiso 1 1 calc R . .
H7C H -0.1158 0.4967 0.7454 0.091 Uiso 1 1 calc R . .
C8 C -0.0288(4) 0.6250(3) 0.7762(3) 0.0414(9) Uani 1 1 d . . .
C9 C -0.1024(4) 0.7060(2) 0.7604(2) 0.0299(8) Uani 1 1 d . . .
C10 C -0.0688(5) 0.7725(3) 0.8229(3) 0.0572(12) Uani 1 1 d . . .
H10 H -0.1050 0.8346 0.8286 0.069 Uiso 1 1 calc R . .
C11 C 0.0268(5) 0.7296(3) 0.8740(3) 0.0521(11) Uani 1 1 d . . .
H11 H 0.0688 0.7583 0.9219 0.063 Uiso 1 1 calc R . .
C12 C -0.2158(5) 0.7178(3) 0.6957(3) 0.0561(12) Uani 1 1 d . . .
H12A H -0.3061 0.7185 0.7252 0.067 Uiso 1 1 calc R . .
H12B H -0.2149 0.6626 0.6570 0.067 Uiso 1 1 calc R . .
C13 C -0.2015(6) 0.8102(4) 0.6423(3) 0.0692(14) Uani 1 1 d . . .
H13 H -0.2623 0.8624 0.6490 0.083 Uiso 1 1 calc R . .
C14 C -0.0871(6) 0.8107(5) 0.5804(4) 0.0776(18) Uani 1 1 d . . .
H14 H -0.0170 0.7637 0.5816 0.093 Uiso 1 1 calc R . .
C15 C -0.0858(5) 0.8907(4) 0.5138(3) 0.0608(13) Uani 1 1 d . . .
H15A H -0.0644 0.9517 0.5418 0.073 Uiso 1 1 calc R . .
H15B H -0.0126 0.8780 0.4715 0.073 Uiso 1 1 calc R . .
C16 C -0.2787(4) 0.8270(3) 0.4170(3) 0.0511(11) Uani 1 1 d . . .
H16 H -0.2332 0.7719 0.3968 0.061 Uiso 1 1 calc R . .
C17 C -0.4127(5) 0.8541(3) 0.4004(3) 0.0474(11) Uani 1 1 d . . .
H17 H -0.4757 0.8202 0.3658 0.057 Uiso 1 1 calc R . .
C18 C -0.3257(5) 0.9648(3) 0.4838(3) 0.0450(10) Uani 1 1 d . . .
C19 C -0.3065(6) 1.0555(4) 0.5341(4) 0.0687(14) Uani 1 1 d . . .
H19A H -0.2397 1.0963 0.5051 0.103 Uiso 1 1 calc R . .
H19B H -0.2722 1.0401 0.5908 0.103 Uiso 1 1 calc R . .
H19C H -0.3953 1.0885 0.5387 0.103 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N4 2.253(3) 4_445 ?
Cd1 N1 2.254(3) . ?
Cd1 O4 2.309(4) 2_664 ?
Cd1 O2 2.325(3) . ?
Cd1 O1 2.429(4) . ?
Cd1 O3 2.491(3) 2_664 ?
Cd1 C6 2.739(4) 2_664 ?
S1 C2 1.713(4) . ?
S1 C5 1.723(4) . ?
O1 C1 1.241(6) . ?
O2 C1 1.259(6) . ?
O3 C6 1.244(5) . ?
O3 Cd1 2.491(3) 2_665 ?
O4 C6 1.262(6) . ?
O4 Cd1 2.309(4) 2_665 ?
N1 C8 1.345(5) . ?
N1 C11 1.366(5) . ?
N3 C18 1.363(6) . ?
N3 C16 1.382(5) . ?
N3 C15 1.469(6) . ?
N4 C18 1.324(5) . ?
N4 C17 1.380(5) . ?
N4 Cd1 2.253(3) 4_454 ?
C1 C2 1.488(6) . ?
C2 C3 1.360(7) . ?
C3 C4 1.409(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.349(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.478(6) . ?
C6 Cd1 2.739(4) 2_665 ?
C7 C8 1.480(6) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.342(5) . ?
C9 C10 1.371(6) . ?
C9 C12 1.477(6) . ?
C10 C11 1.341(6) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.528(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.446(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.512(7) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.349(6) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.488(6) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Cd1 N1 93.95(12) 4_445 . ?
N4 Cd1 O4 139.19(12) 4_445 2_664 ?
N1 Cd1 O4 96.50(13) . 2_664 ?
N4 Cd1 O2 103.39(12) 4_445 . ?
N1 Cd1 O2 141.22(12) . . ?
O4 Cd1 O2 92.56(13) 2_664 . ?
N4 Cd1 O1 126.76(13) 4_445 . ?
N1 Cd1 O1 86.66(11) . . ?
O4 Cd1 O1 93.23(13) 2_664 . ?
O2 Cd1 O1 55.16(12) . . ?
N4 Cd1 O3 85.17(11) 4_445 2_664 ?
N1 Cd1 O3 110.09(12) . 2_664 ?
O4 Cd1 O3 54.20(11) 2_664 2_664 ?
O2 Cd1 O3 105.78(12) . 2_664 ?
O1 Cd1 O3 143.79(12) . 2_664 ?
N4 Cd1 C6 111.91(12) 4_445 2_664 ?
N1 Cd1 C6 103.30(12) . 2_664 ?
O4 Cd1 C6 27.30(13) 2_664 2_664 ?
O2 Cd1 C6 101.89(13) . 2_664 ?
O1 Cd1 C6 119.69(14) . 2_664 ?
O3 Cd1 C6 27.00(11) 2_664 2_664 ?
C2 S1 C5 91.8(2) . . ?
C1 O1 Cd1 88.0(3) . . ?
C1 O2 Cd1 92.3(3) . . ?
C6 O3 Cd1 87.7(2) . 2_665 ?
C6 O4 Cd1 95.7(3) . 2_665 ?
C8 N1 C11 105.5(3) . . ?
C8 N1 Cd1 125.9(3) . . ?
C11 N1 Cd1 124.8(3) . . ?
C18 N3 C16 107.5(3) . . ?
C18 N3 C15 127.3(4) . . ?
C16 N3 C15 124.5(4) . . ?
C18 N4 C17 106.3(3) . . ?
C18 N4 Cd1 130.0(3) . 4_454 ?
C17 N4 Cd1 123.4(3) . 4_454 ?
O1 C1 O2 123.5(4) . . ?
O1 C1 C2 118.5(5) . . ?
O2 C1 C2 117.8(4) . . ?
C3 C2 C1 128.6(4) . . ?
C3 C2 S1 111.1(3) . . ?
C1 C2 S1 119.9(4) . . ?
C2 C3 C4 112.9(4) . . ?
C2 C3 H3 123.5 . . ?
C4 C3 H3 123.5 . . ?
C5 C4 C3 113.0(4) . . ?
C5 C4 H4 123.5 . . ?
C3 C4 H4 123.5 . . ?
C4 C5 C6 130.2(4) . . ?
C4 C5 S1 111.2(3) . . ?
C6 C5 S1 118.4(3) . . ?
O3 C6 O4 122.1(4) . . ?
O3 C6 C5 120.3(4) . . ?
O4 C6 C5 117.6(4) . . ?
O3 C6 Cd1 65.4(2) . 2_665 ?
O4 C6 Cd1 57.0(2) . 2_665 ?
C5 C6 Cd1 170.8(3) . 2_665 ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 109.8(3) . . ?
N1 C8 C7 124.1(4) . . ?
C9 C8 C7 126.1(4) . . ?
C8 C9 C10 108.1(3) . . ?
C8 C9 C12 126.4(4) . . ?
C10 C9 C12 124.9(4) . . ?
C11 C10 C9 106.0(4) . . ?
C11 C10 H10 127.0 . . ?
C9 C10 H10 127.0 . . ?
C10 C11 N1 110.5(4) . . ?
C10 C11 H11 124.7 . . ?
N1 C11 H11 124.7 . . ?
C9 C12 C13 113.3(4) . . ?
C9 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C9 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 115.4(5) . . ?
C14 C13 H13 122.3 . . ?
C12 C13 H13 122.3 . . ?
C13 C14 C15 117.4(5) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 H14 121.3 . . ?
N3 C15 C14 110.8(4) . . ?
N3 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 N3 106.0(4) . . ?
C17 C16 H16 127.0 . . ?
N3 C16 H16 127.0 . . ?
C16 C17 N4 110.0(4) . . ?
C16 C17 H17 125.0 . . ?
N4 C17 H17 125.0 . . ?
N4 C18 N3 110.1(4) . . ?
N4 C18 C19 125.1(4) . . ?
N3 C18 C19 124.7(4) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 995973'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H20 N4 O4 S Zn'
_chemical_formula_weight         453.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.4933(12)
_cell_length_b                   19.380(2)
_cell_length_c                   11.4845(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.559(2)
_cell_angle_gamma                90.00
_cell_volume                     2106.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2741
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      26.38

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    1.295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.674
_exptl_absorpt_correction_T_max  0.792
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8665
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3849
_reflns_number_gt                3097
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0455P)²+0.5686P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3849
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0885
_refine_ls_wR_factor_gt          0.0810
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.058
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.74039(3) 0.545842(13) 0.26590(3) 0.03083(11) Uani 1 1 d . . .
S1 S 0.54052(8) 0.73233(3) -0.07623(6) 0.0431(2) Uani 1 1 d . . .
O1 O 0.6755(3) 0.60222(11) 0.0159(2) 0.0649(7) Uani 1 1 d . . .
O2 O 0.6058(2) 0.61180(10) 0.19564(19) 0.0522(5) Uani 1 1 d . . .
O3 O 0.4414(3) 0.85005(11) -0.2256(2) 0.0776(8) Uani 1 1 d . . .
O4 O 0.3248(2) 0.90470(9) -0.09462(17) 0.0439(5) Uani 1 1 d . . .
N1 N 0.6044(2) 0.47879(10) 0.3337(2) 0.0364(5) Uani 1 1 d . . .
N2 N 0.5157(3) 0.39770(10) 0.4389(2) 0.0441(6) Uani 1 1 d . . .
N3 N 0.4686(2) 0.08539(10) 0.5697(2) 0.0384(5) Uani 1 1 d . . .
N4 N 0.3787(2) 0.00955(10) 0.68433(19) 0.0339(5) Uani 1 1 d . . .
C1 C 0.6138(3) 0.63202(13) 0.0909(3) 0.0400(7) Uani 1 1 d . . .
C2 C 0.5402(3) 0.69794(13) 0.0609(2) 0.0359(6) Uani 1 1 d . . .
C3 C 0.4662(3) 0.73807(15) 0.1311(3) 0.0506(8) Uani 1 1 d . . .
H3 H 0.4542 0.7277 0.2087 0.061 Uiso 1 1 calc R . .
C4 C 0.4093(3) 0.79735(15) 0.0732(3) 0.0492(8) Uani 1 1 d . . .
H4 H 0.3561 0.8303 0.1090 0.059 Uiso 1 1 calc R . .
C5 C 0.4399(3) 0.80129(12) -0.0391(2) 0.0354(6) Uani 1 1 d . . .
C6 C 0.4005(3) 0.85535(13) -0.1279(3) 0.0409(7) Uani 1 1 d . . .
C7 C 0.4602(3) 0.48382(15) 0.3230(3) 0.0519(8) Uani 1 1 d . . .
H7 H 0.4085 0.5162 0.2776 0.062 Uiso 1 1 calc R . .
C8 C 0.4047(3) 0.43445(15) 0.3885(3) 0.0588(9) Uani 1 1 d . . .
H8 H 0.3094 0.4270 0.3974 0.071 Uiso 1 1 calc R . .
C9 C 0.6349(3) 0.42630(13) 0.4049(3) 0.0438(7) Uani 1 1 d . . .
C10 C 0.7789(4) 0.4033(2) 0.4441(4) 0.0974(17) Uani 1 1 d . . .
H10A H 0.8455 0.4385 0.4270 0.146 Uiso 1 1 calc R . .
H10B H 0.8001 0.3616 0.4040 0.146 Uiso 1 1 calc R . .
H10C H 0.7848 0.3950 0.5267 0.146 Uiso 1 1 calc R . .
C11 C 0.5046(4) 0.33858(13) 0.5174(3) 0.0554(9) Uani 1 1 d . . .
H11A H 0.4194 0.3434 0.5581 0.066 Uiso 1 1 calc R . .
H11B H 0.5846 0.3391 0.5755 0.066 Uiso 1 1 calc R . .
C12 C 0.5006(3) 0.26982(13) 0.4550(3) 0.0490(8) Uani 1 1 d . . .
H12A H 0.5867 0.2639 0.4160 0.059 Uiso 1 1 calc R . .
H12B H 0.4214 0.2690 0.3961 0.059 Uiso 1 1 calc R . .
C13 C 0.4859(4) 0.21087(13) 0.5408(3) 0.0514(8) Uani 1 1 d . . .
H13A H 0.5654 0.2121 0.5994 0.062 Uiso 1 1 calc R . .
H13B H 0.4005 0.2177 0.5804 0.062 Uiso 1 1 calc R . .
C14 C 0.4801(3) 0.14063(13) 0.4832(2) 0.0470(7) Uani 1 1 d . . .
H14A H 0.3994 0.1386 0.4259 0.056 Uiso 1 1 calc R . .
H14B H 0.5648 0.1337 0.4426 0.056 Uiso 1 1 calc R . .
C15 C 0.3481(3) 0.05579(12) 0.6002(2) 0.0361(6) Uani 1 1 d . . .
C16 C 0.2048(3) 0.07095(17) 0.5475(3) 0.0616(9) Uani 1 1 d . . .
H16A H 0.1414 0.0351 0.5676 0.092 Uiso 1 1 calc R . .
H16B H 0.2063 0.0733 0.4641 0.092 Uiso 1 1 calc R . .
H16C H 0.1735 0.1143 0.5765 0.092 Uiso 1 1 calc R . .
C17 C 0.5224(3) 0.01093(13) 0.7073(3) 0.0406(7) Uani 1 1 d . . .
H17 H 0.5731 -0.0162 0.7627 0.049 Uiso 1 1 calc R . .
C18 C 0.5790(3) 0.05742(14) 0.6377(3) 0.0452(7) Uani 1 1 d . . .
H18 H 0.6742 0.0684 0.6361 0.054 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O2 1.9375(18) . ?
Zn1 O4 1.9805(19) 4_676 ?
Zn1 N4 1.987(2) 4_665 ?
Zn1 N1 2.030(2) . ?
S1 C2 1.710(3) . ?
S1 C5 1.717(3) . ?
O1 C1 1.224(3) . ?
O2 C1 1.273(3) . ?
O3 C6 1.221(3) . ?
O4 C6 1.273(3) . ?
O4 Zn1 1.9805(19) 4_575 ?
N1 C9 1.323(3) . ?
N1 C7 1.369(3) . ?
N2 C9 1.346(3) . ?
N2 C8 1.362(4) . ?
N2 C11 1.467(3) . ?
N3 C15 1.351(3) . ?
N3 C18 1.369(4) . ?
N3 C14 1.471(3) . ?
N4 C15 1.333(3) . ?
N4 C17 1.368(3) . ?
N4 Zn1 1.987(2) 4_566 ?
C1 C2 1.484(4) . ?
C2 C3 1.356(4) . ?
C3 C4 1.413(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.345(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.489(4) . ?
C7 C8 1.350(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.473(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.512(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.522(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.513(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.473(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.345(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Zn1 O4 103.21(9) . 4_676 ?
O2 Zn1 N4 126.78(9) . 4_665 ?
O4 Zn1 N4 113.75(8) 4_676 4_665 ?
O2 Zn1 N1 99.42(9) . . ?
O4 Zn1 N1 103.19(9) 4_676 . ?
N4 Zn1 N1 107.40(9) 4_665 . ?
C2 S1 C5 91.87(13) . . ?
C1 O2 Zn1 120.63(18) . . ?
C6 O4 Zn1 108.81(17) . 4_575 ?
C9 N1 C7 106.2(2) . . ?
C9 N1 Zn1 127.93(19) . . ?
C7 N1 Zn1 125.59(18) . . ?
C9 N2 C8 107.5(2) . . ?
C9 N2 C11 127.1(3) . . ?
C8 N2 C11 125.4(3) . . ?
C15 N3 C18 108.1(2) . . ?
C15 N3 C14 126.5(2) . . ?
C18 N3 C14 125.4(2) . . ?
C15 N4 C17 106.5(2) . . ?
C15 N4 Zn1 126.18(19) . 4_566 ?
C17 N4 Zn1 127.25(17) . 4_566 ?
O1 C1 O2 126.0(3) . . ?
O1 C1 C2 119.1(3) . . ?
O2 C1 C2 115.0(2) . . ?
C3 C2 C1 127.8(3) . . ?
C3 C2 S1 111.3(2) . . ?
C1 C2 S1 120.9(2) . . ?
C2 C3 C4 112.5(3) . . ?
C2 C3 H3 123.7 . . ?
C4 C3 H3 123.7 . . ?
C5 C4 C3 113.2(3) . . ?
C5 C4 H4 123.4 . . ?
C3 C4 H4 123.4 . . ?
C4 C5 C6 129.4(2) . . ?
C4 C5 S1 111.1(2) . . ?
C6 C5 S1 119.5(2) . . ?
O3 C6 O4 124.6(3) . . ?
O3 C6 C5 119.3(3) . . ?
O4 C6 C5 116.1(2) . . ?
C8 C7 N1 109.4(3) . . ?
C8 C7 H7 125.3 . . ?
N1 C7 H7 125.3 . . ?
C7 C8 N2 106.5(3) . . ?
C7 C8 H8 126.7 . . ?
N2 C8 H8 126.7 . . ?
N1 C9 N2 110.4(2) . . ?
N1 C9 C10 125.0(3) . . ?
N2 C9 C10 124.6(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 113.4(3) . . ?
N2 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
N2 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 110.8(3) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 113.2(3) . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.8 . . ?
N3 C14 C13 111.2(2) . . ?
N3 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
N3 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N4 C15 N3 109.4(2) . . ?
N4 C15 C16 125.0(3) . . ?
N3 C15 C16 125.6(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 N4 109.8(2) . . ?
C18 C17 H17 125.1 . . ?
N4 C17 H17 125.1 . . ?
C17 C18 N3 106.2(2) . . ?
C17 C18 H18 126.9 . . ?
N3 C18 H18 126.9 . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 995974'
